It is often desirable to determine whether an agricultural machine is in proximity to a point of interest. In prior art tracking arrangements a stationary geofence would be created about a point of interest and if a tracked vehicle crossed the stationary geofence, then an alert would issue. While such systems are suitable for their intended purpose, they have several drawbacks, due at least in part to their reliance upon a stationary geofence. For example, there may be points of interest that, like the machine being tracked, are mobile. For example, it may be desirable to determine the proximity of a moving agricultural vehicle with another moving agricultural vehicle, weather pattern, or the like. In addition, such prior art systems often lack the ability to identify the particular points of interest and provide an intelligent alert that considers characteristics of the machine being tracked and/or the point of interest.